Introducing My Dominant Boyfriend to Pegging for the First Time

How I introduced my masculine boyfriend to pegging

I’ve always wanted to try pegging with very rugged boyfriend Ryan, but have always been afraid to ask him to try it. Ryan is such a rough and rugged man I always assumed there was no way in hell he would let me fuck him in the ass. Last week, we were laying in bed after a long night of drinking and fucking, I finally got the courage to ask him what he thought about pegging. Reaching under the covers, I rubbed Ryan’s cock and asked “Babe, would you ever let me fuck your ass?” Ryan laughed, “Maybe.” He replied “ I’ve always been curious to know what it would feel like to be penetrated. And I hear prostate play is fantastic”. I sat up in bed, shocked that he had giving pegging this much thought. “So, you would be down to try pegging?” I asked, trying to hide how excited I was. “Sure.” Ryan replied, “I just wouldn’t want to know it was coming, I would want it to be a surprise so that I couldn’t back out of the experience.” As we drifted off to sleep began formulating a plan to introduce Ryan to pegging.

Fast forward a week later, called Ryan and told him to meet me at the Beverly Hilton Hotel after work instead of going home. I told Ryan to meet me in the room at 5 PM, but I left him waiting for me until 5:30 PM. I wanted him to get nervous wondering what to expect when I arrived. Ryan’s face lit up as I walking into the room wearing his favorite, curve hugging mini dress; his happy expression quickly turned to confusion when he noticed the bulge underneath my mini dress.

Ryan was sitting on the bed staring at the bulge in my dress. Standing in front of him, I slowly pulled my dress to show him the 8-inch strap-on the cock I was wearing. “Why aren’t you getting my cock ready for you?” I asked with a smile. I pushed Ryan’s head down towards my cock, and his mouth dropped open without any resistance. From the way Ryan slurped that cock down his throat, I could tell that this was something he had been thinking about for a long time. Once Ryan got my cock dripping wet with his mouth, I laid him back on the bed and took off his pants as he slowly removed his shirt. Ryan began stroking his cock as I spread his legs and began to tongue his virgin asshole.

With Ryan’s legs spread and his pink asshole ready, I stood up and started slowly working my 8-inch strap-on cock into Ryan’s ass. He was tense at first, but it didn’t take long for him to relax and give in to the joys of being fucked. I took long, deep strokes, making sure that I wy cock was hitting his prostate. Ryan’s rock hard cock twitched and jumped with every stroke. The rivets on the strap teased my clit as I fucked Ryan. But it was seeing my usually masculine, dominant boyfriend laying back, spread open for dick that was the biggest turn on. I knew that pegging Ryan would be fun, but I never thought it would be this hot. I pulled Ryan’s legs up towards my shoulders as I fucked him harder, and deeper. Ryan stroked his cock hard and fast as I pounded his asshole. I could see the head of his cock throbbing; I knew he was getting close. I shoved my cock in as deep as I could and began grinding against his prostate. Ryan’s cock exploded! His cum was shooting all over his chest and shoulders.

After Ryan had cum, I crawled on top of him, his hot thick cum covering my tits as I laid on top of him. I kissed Ryan as I rubbed my wet pussy against his till throbbing cock. “Are you ready for round two?” I asked, slowly working the head of Ryan’s cock into me. As Ryan began to slide into me, I know that this would not be the last time that Ryan and I experimented with pegging.